CN105482373A - Method for toughening and modifying epoxy resin through epoxy-terminated polystyrene low polymer - Google Patents
Method for toughening and modifying epoxy resin through epoxy-terminated polystyrene low polymer Download PDFInfo
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- CN105482373A CN105482373A CN201610009876.1A CN201610009876A CN105482373A CN 105482373 A CN105482373 A CN 105482373A CN 201610009876 A CN201610009876 A CN 201610009876A CN 105482373 A CN105482373 A CN 105482373A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Abstract
The invention provides a method for toughening and modifying epoxy resin through epoxy-terminated polystyrene low polymer. The method includes the steps that firstly a reactive toughening agent PSG is prepared, and then all raw materials are mixed and stirred for 1-2 hours; the mixture is poured into a die which is preheated ready, vacuumizing is conducted to remove bubbles, curing is conducted for 2-3 hours at the temperature of 80-100 DEG C, then curing is conducted for 2-3 hours at the temperature of 100-120 DEG C, finally curing is conducted for 3-4 hours at the temperature of 120-150 DEG C, demoulding is conducted after cooling, and a modified epoxy resin casting body is obtained; the raw materials comprise, by weight, 100 parts of epoxy resin, 2-15 parts of the reactive toughening agent PSG, 80-95 parts of a curing agent and 1-3 parts of curing accelerator. Compared with traditional epoxy resin which is toughened by liquid rubber, the anti-impact performance of the epoxy resin toughened and modified through the method is improved, and the epoxy resin maintains the good mechanical property and heat resistance, further has the advantages of being low in cost, stable in performance, good in compatibility between the toughening agent and an epoxy/anhydride system and the like and can serve as a composite material base body, a coating, an electronic packaging material and the like to be used in the fields of electronics, electrical engineering, space flight and aviation, communication and transportation, buildings and the like.
Description
Technical field
The present invention relates to Material Field, especially relate to a kind of preparation method of epoxy terminated polystyrene oligopolymer Toughening Modification of Epoxy.
Background technology
Bisphenol A type epoxy resin is a kind of universal thermosetting resin, have excellent mechanical property, adhesiveproperties, chemical stability and electrical insulation capability, Chang Zuowei matrices of composite material, tackiness agent, coating, electronic package material etc. are widely used in the fields such as aerospace, electronic apparatus, communications and transportation and building.Why epoxy resin shows excellent mechanical property, have benefited from the high-crosslinking-degree of curing system, but the too high meeting of cross-linking density makes epoxy resin lacking toughness, and impact resistance and resistance to cracking can be poor, limit the range of application of epoxy resin.
The method for toughening of current epoxy resin mainly comprise rubber toughened, Toughened With High Performance Thermoplastics, Rigid Particles Toughened, interact network method are toughness reinforcing, core-shell particles polymer toughening, liquid crystalline polymers are toughness reinforcing.As with amino terminated liquid nitrile rubber (Amino-terminatedliquidnitrilerubber, be called for short ATBN) and carboxyl end of the liquid acrylonitrile-butadiene rubber (Carboxylated-terminatedliquidnitrilerubber, be called for short CTBN) etc. band active group (hydroxyl, carboxyl, amino etc.) liquid rubber modified epoxy resin, its active end group can react with epoxy resin or solidifying agent and generate covalent linkage, improve consistency and the interface binding power of rubber particles and resin matrix, remarkable lifting impelling strength and tension set, but physical strength and thermotolerance sacrifice larger.Polymkeric substance with epoxy group(ing) is applied more and more wider in Toughening Epoxy Resin, and such polymer architecture contains soft segment and active group, and make the destruction of epoxy resin change ductile rupture into by brittle rupture, impelling strength is significantly improved.Epoxy terminated polystyrene polymkeric substance is often used as reactive compatibilizer and bioid enzyme carrier, it can be used as toughner to have no report to the toughness and over-all properties that improve epoxy resin.
Summary of the invention
The technical problem that will solve required for the present invention is: the preparation method providing a kind of epoxy terminated polystyrene oligopolymer Toughening Modification of Epoxy, solves epoxy resin roughening and does not strengthen and toughness reinforcing heat labile technical barrier.
The present invention solves its technical problem and adopts following technical scheme:
The method of a kind of epoxy terminated polystyrene oligopolymer Toughening Modification of Epoxy provided by the invention, specifically: first prepare endurable active toughener PSG, then mixes all raw materials, stirs 1-2 hour; Mixture is poured in preheated mould, vacuumize 30 minutes and remove bubble, at 80-100 DEG C of solidification 2-3 hour, then at 100-120 DEG C of solidification 2-3 hour, finally at 120-150 DEG C of solidification 3-4 hour, after cooling, namely the demoulding obtains described modified epoxy casting matrix; Described raw material is epoxy resin 100 parts, endurable active toughener PSG2-15 part, solidifying agent 80-95 part, and curing catalyst 1-3 part, is weight part.
Described endurable active toughener PSG, obtained by the material of following weight parts: by vinylbenzene 40-60 part, hexanaphthene 210-240 part and the mixing of tetrahydrofuran (THF) 2-11 part, reaction system is made to be faint yellow with a small amount of n-Butyl Lithium removal of impurities and colour-fast in 2-3 minute, add n-Butyl Lithium 5-25 part, at 0-10 DEG C of isothermal reaction 1-2 hour; Add glycidyl methacrylate 17-75 part, at 20-30 DEG C of isothermal reaction 1-2 hour, omnidistance argon shield; Add methyl alcohol 1-7 part and stop polyreaction, after separation and purification, namely obtain described endurable active toughener PSG oligopolymer.
In aforesaid method, can the reaction product that termination polyreaction obtains be joined in dehydrated alcohol, white flock precipitate thing is obtained through suction filtration, with dehydrated alcohol, throw out is washed suction filtration twice again, removing unreacted monomer and organic solvent, until constant weight, gained white powder was target product PSG in dry 12-18 hour under 55 DEG C of conditions to be placed in vacuum drying oven.
The number-average molecular weight of described endurable active toughener PSG is 2500-5600, and molecular weight distribution width is 1.2-2.2.
The number-average molecular weight of described endurable active toughener PSG and composition regulate and control by changing monomer ratio, meet the needs of multiple result of use.
Described epoxy resin is bisphenol A-type Racemic glycidol ethers E-51 epoxy resin, E-53 epoxy resin or E-44 epoxy resin.
Described solidifying agent is one or more in methyl tetrahydro phthalic anhydride, methyl hexahydrophthalic anhydride, methylnadic anhydride.
Described curing catalyst is 2,4,6-tri-(dimethylamino methyl) phenol, imidazoles or quaternary ammonium salt.
Epoxy terminated polystyrene oligopolymer Toughening Modification of Epoxy prepared by the present invention, it is as matrices of composite material, gluing or electronic package material, can be applicable to comprise the fields such as electric, space flight and aviation, communications and transportation, building.
Method for toughening of the present invention, compared with traditional method for toughening, has following main advantage:
(1) molecular weight of endurable active toughener PSG and composition controlled, technique is simple, and first for Toughening Modification of Epoxy.
(2) a large amount of reactive epoxy groups of PSG can be reacted with the anhydride group in acid anhydride type curing agent and be generated covalent linkage, introduce a large amount of soft segment, the shock resistance of remarkable enhancing ring epoxy resins in the cross-linked network of epoxy/anhydride-cured system.
(3) very well, toughening effect is stablized for PSG and epoxy/anhydride system consistency.
(4) benzene ring structure of PSG side base can provide rigidity for epoxy resin, while raising modified epoxy impelling strength, keep good physical strength and thermotolerance.
Accompanying drawing explanation
Fig. 1 is the SEM photo of unmodified epoxy resin casting matrix impact fracture surface.
Fig. 2 is the SEM photo of PSG Toughening Modification of Epoxy casting matrix impact fracture surface.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in detail.Following examples are also non exhaustive, do not do any restriction to the present invention.
The Structure and Properties test related in following embodiment is carried out as follows:
(1) shock strength: adopt the test of XJJD-50 type electronics impact tester for simple supported beam.
(2) mechanical property: adopt the test of RGE-30A type microcomputer control All Digital Electronic universal testing machine.
(3) cross-section morphology: adopt JSM-IT300 type sem observation.
(4) resistance toheat: adopt XWB-300A type thermal distortion-vicat softening point temperature determinator test.
Embodiment 1
(1) preparation of endurable active toughener PSG:
Quality group is become vinylbenzene 52g, hexanaphthene 223.5g, tetrahydrofuran (THF) 10.8g joins in a reactor with agitator, thermometer, reflux and logical argon gas device, the removal of impurities of 2mL n-butyllithium solution is added with syringe, reaction system is faint yellow and colour-fast in 2-3 minute, add n-Butyl Lithium 22.7mL, adopt in ice-water bath 0 DEG C of isothermal reaction 2 hours; Add glycidyl methacrylate 71g, carry out reaction 2 hours at 25 DEG C, omnidistance argon shield.Question response terminates, add methyl alcohol 6.4mL and stop polyreaction, mixed solution is poured in a large amount of dehydrated alcohols, suction filtration obtains white flock precipitate thing, with dehydrated alcohol, throw out is washed suction filtration twice again, removing unreacted monomer and each organic solvent, be placed in vacuum drying oven under 55 DEG C of conditions dry 12 hours until constant weight, gained white powder is target product, and its number-average molecular weight is 2500.
(2) preparation of endurable active toughener PSG modified epoxy:
E-53 epoxy resin 100g, endurable active toughener 2g, methyl hexahydrophthalic anhydride 80g, imidazoles 2g are added in the reactor with agitator and thermometer, 1 hour is uniformly mixed at 60 DEG C, mixture is poured in preheated particular mold, vacuumize 30 minutes and remove bubble, 80 DEG C of solidifications 2 hours, then 100 DEG C of solidifications 2 hours, finally 140 DEG C of solidifications 4 hours, after cooling, namely the demoulding obtains modified epoxy casting matrix.
Embodiment 2
(1) preparation of endurable active toughener PSG:
Quality group is become vinylbenzene 52g, hexanaphthene 223.5g, tetrahydrofuran (THF) 5.4g joins in a reactor with agitator, thermometer, reflux and logical argon gas device, the removal of impurities of 2mL n-butyllithium solution is added with syringe, reaction system is faint yellow and colour-fast in 2-3 minute, add n-Butyl Lithium 11.4mL, adopt in ice-water bath 0 DEG C of isothermal reaction 2 hours; Add glycidyl methacrylate 35.5g, carry out reaction 2 hours at 25 DEG C, omnidistance argon shield.Question response terminates, add methyl alcohol 3.2mL and stop polyreaction, mixed solution is poured in a large amount of dehydrated alcohols, suction filtration obtains white flock precipitate thing, with dehydrated alcohol, throw out is washed suction filtration twice again, removing unreacted monomer and each organic solvent, be placed in vacuum drying oven under 55 DEG C of conditions dry 12 hours until constant weight, gained white powder is target product, and its number-average molecular weight is 3500.
(2) preparation of endurable active toughener PSG modified epoxy:
By E-51 epoxy resin 100g, endurable active toughener 7g, methyl tetrahydro phthalic anhydride 85g, 2,4,6-tri-(dimethylamino methyl) phenol 2g adds in the reactor with agitator and thermometer, be uniformly mixed 1 hour at 60 DEG C, mixture is poured in preheated particular mold, vacuumize 30 minutes and remove bubble, 100 DEG C of solidifications 2 hours, then 120 DEG C of solidifications 2 hours, finally 150 DEG C of solidifications 4 hours, after cooling, namely the demoulding obtains modified epoxy casting matrix.
Embodiment 3
(1) preparation of endurable active toughener PSG:
Quality group is become vinylbenzene 52g, hexanaphthene 223.5g, tetrahydrofuran (THF) 2.7g joins in a reactor with agitator, thermometer, reflux and logical argon gas device, the removal of impurities of 2mL n-butyllithium solution is added with syringe, reaction system is faint yellow and colour-fast in 2-3 minute, add n-Butyl Lithium 5.7mL, adopt in ice-water bath 0 DEG C of isothermal reaction 2 hours; Add glycidyl methacrylate 17.8g, carry out reaction 2 hours at 25 DEG C, omnidistance argon shield.Question response terminates, add methyl alcohol 1.6mL and stop polyreaction, mixed solution is poured in a large amount of dehydrated alcohols, suction filtration obtains white flock precipitate thing, with dehydrated alcohol, throw out is washed suction filtration twice again, removing unreacted monomer and each organic solvent, be placed in vacuum drying oven under 55 DEG C of conditions dry 12 hours until constant weight, gained white powder is target product, and its number-average molecular weight is 5600.
(2) preparation of endurable active toughener PSG modified epoxy:
By E-51 epoxy resin 100g, endurable active toughener 15g, methyl tetrahydro phthalic anhydride 90g, 2,4,6-tri-(dimethylamino methyl) phenol 3g adds in the reactor with agitator and thermometer, be uniformly mixed 1 hour at 60 DEG C, mixture is poured in preheated particular mold, vacuumize 30 minutes and remove bubble, 100 DEG C of solidifications 2 hours, then 120 DEG C of solidifications 2 hours, finally 150 DEG C of solidifications 4 hours, after cooling, namely the demoulding obtains modified epoxy casting matrix.
Comparative example:
By E-51 epoxy resin 100g, methyl tetrahydro phthalic anhydride 85g, 2,4,6-tri-(dimethylamino methyl) phenol 3g adds in the reactor with agitator and thermometer, is uniformly mixed 1 hour, is poured into by mixture in preheated particular mold at 60 DEG C, vacuumize 30 minutes and remove bubble, 100 DEG C of solidifications 2 hours, then 120 DEG C of solidifications 2 hours, finally 150 DEG C of solidifications 4 hours, after cooling, namely the demoulding obtains pure epoxy resin casting matrix, as check sample.
Prepared by the Toughening Modification of Epoxy prepared by embodiment 1-3 and comparative example not epoxy resin toughenedly carries out contrast test, and test result is in table 1.
From experimental result described in table 1, adopt endurable active toughener PSG toughening-modifiedepoxy resin material, toughness be improved significantly, shock strength comparatively pure epoxy resin improves 70.1%-139%, the mechanical property that retaining ring epoxy resins is good simultaneously, resistance toheat slightly declines.
As shown in Figure 1, the section flat smooth of pure epoxy resin casting matrix is brittle rupture; As shown in Figure 2, endurable active toughener PSG particle is dispersed in resin matrix, and under stress, bring out crackle and stop the expansion of crackle, the section of Toughening Modification of Epoxy casting matrix is more coarse and tomography is more, in ductile rupture.
Technique scheme provided by the invention, molecular weight and the controlled response type oligopolymer PSG of composition are used for Toughening Epoxy Resin first, there is toughening effect obvious, keep the advantage of good mechanical strength and thermotolerance simultaneously, solve epoxy resin roughening not strengthen and toughness reinforcing heat labile technical barrier, can be used as matrices of composite material, tackiness agent, coating, electronic package material etc. and be widely used in the fields such as aerospace, electronic apparatus, communications and transportation and building.
Table 1PSG Toughening Modification of Epoxy compares with not epoxy resin toughened properties
Claims (9)
1. a method for epoxy terminated polystyrene oligopolymer Toughening Modification of Epoxy, is characterized in that first preparing endurable active toughener PSG, is then mixed by all raw materials, stirs 1-2 hour; Mixture is poured in preheated mould, vacuumize 30 minutes and remove bubble, at 80-100 DEG C of solidification 2-3 hour, then at 100-120 DEG C of solidification 2-3 hour, finally at 120-150 DEG C of solidification 3-4 hour, after cooling, namely the demoulding obtains described modified epoxy casting matrix; Described raw material is epoxy resin 100 parts, endurable active toughener PSG2-15 part, solidifying agent 80-95 part, and curing catalyst 1-3 part, is weight part.
2. method according to claim 1, it is characterized in that described endurable active toughener PSG, obtained by the material of following weight parts: by vinylbenzene 40-60 part, hexanaphthene 210-240 part and the mixing of tetrahydrofuran (THF) 2-11 part, reaction system is made to be faint yellow with a small amount of n-Butyl Lithium removal of impurities and colour-fast in 2-3 minute, add n-Butyl Lithium 5-25 part, at 0-10 DEG C of isothermal reaction 1-2 hour; Add glycidyl methacrylate 17-75 part, at 20-30 DEG C of isothermal reaction 1-2 hour, omnidistance argon shield; Add methyl alcohol 1-7 part and stop polyreaction, after separation and purification, namely obtain described endurable active toughener PSG oligopolymer.
3. method according to claim 2, it is characterized in that: the reaction product that termination polyreaction obtains is joined in dehydrated alcohol, white flock precipitate thing is obtained through suction filtration, with dehydrated alcohol, throw out is washed suction filtration twice again, removing unreacted monomer and organic solvent, until constant weight, gained white powder was target product PSG in dry 12-18 hour under 55 DEG C of conditions to be placed in vacuum drying oven.
4. method according to claim 2, is characterized in that: the number-average molecular weight of described endurable active toughener PSG is 2500-5600, and molecular weight distribution width is 1.2-2.2.
5. method according to claim 3, is characterized in that: the number-average molecular weight of described endurable active toughener PSG and composition regulate and control by changing monomer ratio, meet the needs of multiple result of use.
6. method according to claim 1, is characterized in that: described epoxy resin is bisphenol A-type Racemic glycidol ethers E-51 epoxy resin, E-53 epoxy resin or E-44 epoxy resin.
7. method according to claim 1, is characterized in that: described solidifying agent is one or more in methyl tetrahydro phthalic anhydride, methyl hexahydrophthalic anhydride, methylnadic anhydride.
8. method according to claim 1, is characterized in that: described curing catalyst is 2,4,6-tri-(dimethylamino methyl) phenol, imidazoles or quaternary ammonium salt.
9. method according to claim 1, is characterized in that: described modified epoxy can be used as matrices of composite material, coating or electronic package material, is applied to and comprises electric, space flight and aviation, communications and transportation, building field.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN110105709A (en) * | 2019-03-06 | 2019-08-09 | 武汉理工大学 | The method of toughening agent modified epoxy resin toughness |
CN114456410A (en) * | 2022-01-12 | 2022-05-10 | 东华大学 | High-performance epoxy resin toughening agent for winding and forming of composite material and preparation method thereof |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110105709A (en) * | 2019-03-06 | 2019-08-09 | 武汉理工大学 | The method of toughening agent modified epoxy resin toughness |
CN114456410A (en) * | 2022-01-12 | 2022-05-10 | 东华大学 | High-performance epoxy resin toughening agent for winding and forming of composite material and preparation method thereof |
CN114456410B (en) * | 2022-01-12 | 2023-09-05 | 东华大学 | High-performance epoxy resin toughening agent for winding and forming composite material and preparation method thereof |
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